Wilco's music has been inspired by a wide variety of artists and styles, including Bill Fay and Television, and has in turn influenced music by The National and Cherry Ghost. The band continued in the alternative country of Uncle Tupelo on its debut album A.M. (1995), but has since introduced more experimental aspects to their music.

Wilco garnered media attention for its fourth album, Yankee Hotel Foxtrot (2002), and the controversy surrounding it. After the recording sessions were complete, Reprise Records rejected the album and dismissed Wilco from the label. As part of a buy-out deal, Reprise gave Wilco the rights to the album for free. After streaming Foxtrot on its website, Wilco sold the album to Nonesuch Records in 2002. Both record labels are subsidiaries of Warner Music Group, leading one critic to say that the album showed "how screwed up the music business in the early twenty-first century." Yankee Hotel Foxtrot is Wilco's most successful release to date, selling over 590,000 copies. Wilco won two Grammy Awards for their fifth studio album, 2004's A Ghost Is Born, including Best Alternative Music Album.

Wilco was formed following the breakup of the influential alternative country music group Uncle Tupelo. Singer Jay Farrar quit the band in 1994 supposedly because of a soured relationship with co-singer Jeff Tweedy. Both Tweedy and Farrar sought to form bands immediately after the breakup. Tweedy was able to keep the entire Uncle Tupelo lineup sans Farrar, including bassist John Stirratt, drummer Ken Coomer, and multi-instrumentalist Max Johnston. The band was tempted to keep the Uncle Tupelo name, but ultimately decided to rename the band. The group named itself "Wilco" after the CB radio voice procedure for "I Will Comply".

A.M. and Being There

After collaborating with Syd Straw on a cover version of the Ernest Tubb song, "The T.B. is Whipping Me" (released in September 1994 on the Red Hot + Country compilation), Wilco began recording tracks for A.M., their first studio album, at Easley studio in June 1995. A demo tape from these recordings was sent to executives at Reprise Records, a subsidiary of Warner Brothers, and the label signed Tweedy to a contract. Although Tweedy stated that he wanted a more collaborative project than Uncle Tupelo, only his name appeared on the Reprise contract. Tweedy requested songwriting submissions from other members, but only one submission—John Stirratt's "It's Just That Simple"—appeared on A.M.. It was the last song Wilco ever released that was solely written by a member besides Tweedy.

Stylistically similar to Uncle Tupelo, the music on A.M. was considered to be straightforward alternative country rock in what Tweedy later described as "trying to tread some water with a perceived audience." A.M. peaked at number twenty-seven on the Billboard Heatseekers chart, considerably lower than the debut album of Jay Farrar's new band, Son Volt. The album was met with modest reviews though it would rank thirty-fourth in the Village Voice's 1995 Pazz & Jop critics poll. Critically and commercially paling in comparison to the reception of Son Volt's album, the Wilco members perceived A.M. to be a failure. Shortly after the release of the album, multi-instrumentalist Jay Bennett joined the band, providing the band with a keyboardist and another guitarist.

Wilco made its live debut on November 17, 1994 to a capacity crowd at Cicero's Basement Bar in St. Louis, Missouri (the band was billed for the occasion as "Black Shampoo").

During the two hundred-date tour supporting A.M., Tweedy began to write songs for a second album. The lyrical theme of the songs reflected a relationship between musical artist and a listener; Tweedy chose this topic because he sought to eschew the alternative country fan base. Ken Coomer elaborated:

"The whole No Depression thing was funny to us because people seemed to forget that Jeff was a bigger punk-rock fan than a country fan. It led to things like us all switching instruments on 'Misunderstood,' where I'm playing guitar."

A number of songs were recorded with this theme, including "Sunken Treasure" and "Hotel Arizona", however, Wilco also recorded a number of songs in the style of A.M. Wilco named the album Being There after a Peter Sellers film of the same name. The band went through some personnel changes during the recording sessions. Max Johnston left the band because he felt that his role in the band had diminished in favor of Bennett; he had also been replaced by violinist Jesse Greene on one track because the band felt that Johnston was unable to play the part. Bob Egan of Freakwater briefly joined the band in the studio, playing pedal steel guitar on "Far, Far Away" and "Dreamer in My Dreams", and then became an official member in September 1996.

Unlike the A.M. recording sessions, the band had no vocation for producing a hit song from their second effort. The recording sessions produced nineteen songs, too many for a single album release. Tweedy was concerned about the high retail price that a double album would be sold for (at least $30), so he asked Reprise Records to release it as a double album at a single album price ($17.98 or less). Reprise agreed to this on the terms that they received Wilco's share of the album royalties. It was estimated in 2003 that the band lost almost $600,000 on the deal, but Tweedy was satisfied. Being There was well-received by critics from several major media outlets, including Rolling Stone. The album reached #73 on the Billboard album charts, a significant improvement from A.M., and placed fourteenth on the Pazz & Jop Critics Poll for 1996.

Summerteeth and the Mermaid Avenue sessions

In November 1997, Wilco entered Willie Nelson's recording studio in Spicewood, Texas to record a third studio album. The album was lyrically inspired by the marital problems of Tweedy and his wife, as well as by twentieth-century literature. Tweedy relied heavily on Bennett to provide music for the singer's "bold, but depressing" lyrics. Wilco recorded several songs, including "Via Chicago" and "She's a Jar," but began working on another project before assembling the tracks into an album.

Nora Guthrie contacted singer-songwriter Billy Bragg in spring 1995 about recording some unreleased songs by her father, folk singer Woody Guthrie. Most of the songs were written late in Guthrie's life when he was unable to record due to the motor impairments of Huntington's disease. By the 1990s, Woody Guthrie had become a "relic" to the MTV generation, and Nora sought to establish a different legacy for the musician. To Nora, Bragg was "the only singer I knew taking on the same issues as Woody." Bragg was concerned, however, that his fans would not realize that the songs were written by Guthrie when he performed them on tour, so he decided to record the album with another band.

Bragg contacted Tweedy and Bennett about co-recording the album while Wilco was on the European segment of their Being There tour. Bragg was particularly fond of Being There because their influences extended farther back than the 1950s. Although Tweedy was indifferent to the offer, Bennett was enthused about recording songs of one of his idols—Bennett's previous band Titanic Love Affair was named after a Billy Bragg lyric. A recording contract between Bragg and Wilco was signed after a show at Shepherd's Bush Empire. Bragg mostly recorded the politically-charged lyrics, while Tweedy preferred to record lyrics that showcased Guthrie as a "freak weirdo." The recording of Mermaid Avenue began on December 12, 1997, and was the topic of BBC's Man in the Sand documentary film.

Tempers flared between Bragg and Wilco after the album was completed. Bennett believed that Bragg was overproducing his songs, a sharp contrast to Wilco's sparser contributions. Bennett called Bragg about the possibility of remixing Bragg's songs, to which Bragg responded with "you make your record, and I'll make mine, fucker." Eventually Bragg sent copies of his recordings to Chicago for Bennett to remix, but Bragg refused to use the new mixes on the album. The two parties were unable to establish a promotional tour and quarreled over royalties and guest musician fees.

Despite these conflicts, the album was released on June 23, 1998, and sold over 277,000 copies. The album received rave reviews from Robert Christgau and Rolling Stone, and was nominated for a Grammy Award for Best Contemporary Folk Album. It also placed fourth on the Pazz & Jop critics poll for 1998. After the album was released, Bob Egan was replaced by multi-instrumentalist Leroy Bach.

After the completion of the Mermaid Avenue sessions, Wilco returned to Spicewood to complete their third studio album, Summerteeth. Unlike previous Wilco and Uncle Tupelo recordings, the album featured a lot of overdubbing with Pro Tools. Stirratt and Coomer were concerned with the production, since it reduced their involvement in the music. According to Stirratt:

"The story of Summerteeth is Jay bought a Mellotron and he was going to use it, no matter what. It was lovely, but it was overdone. Once they got going on the overdubs, they didn't stop. And nobody in the band stepped up to stop the madness … It reminds me of Heart of Darkness, where you knowingly extend the creative process for the purpose of exploration or redemption, or whatever it is you're looking for."

During 1999, Warner Brothers was looking to help repay a $16 billion debt acquired during the recent merger of parent company Warner Communications with Time Inc.. As a result, Warner's imprints were under pressure to produce musical acts that would yield hit records. The head of Reprise, Howie Klein, who had previously authorized the release of Being There as a double album, was willing to let Wilco produce Summerteeth without label input. When Klein played the album for Reprise's A&R department, however, they demanded a radio single for the album. Wilco agreed to do this "once and once only" and recorded a radio-friendly version of "Can't Stand It" at the request of David Kahne, the head of the A&R department. The single version of "Can't Stand It" failed to cross over from Triple-A radio to alternative rock stations. Consequently, the album sold only 200,000 copies, significantly less than Being There. This was despite critical acclaim; the album placed eighth on the Pazz & Jop critics' poll for 1999.

After the release of Summerteeth, the band resumed the Mermaid Avenue sessions. Although they had recorded enough material for a second release in 1998, Wilco recorded a few new songs for Mermaid Avenue Vol. II. "Someday Some Morning Sometime," featuring a vibraphone filtered through a space echo, was identified by Tweedy as being the "piece to the puzzle" towards the creation of their fourth studio album. The album was released on May 30, 2000, and was the last release from the sessions.

Yankee Hotel Foxtrot

Shortly after the recording sessions for Mermaid Avenue Vol. II, Wilco purchased a studio in Irving Park, Chicago, which they named the Wilco Loft. The band recorded some tracks in the studio in early 2000 for a fourth studio album. In May 2000, Jeff Tweedy requested to perform with Jim O'Rourke at a festival in Chicago; Tweedy was a fan of O'Rourke's Bad Timing. O'Rourke introduced Tweedy to drummer Glenn Kotche, and the trio enjoyed working together so much that they decided to record an album as a side project named Loose Fur. Wilco had recorded an entire album of music at this point, but Tweedy was unhappy with the drum parts. He enjoyed Kotche's contributions to Loose Fur so much that Tweedy brought him into the studio to re-record some demos. Some believe that Tweedy sought to make Wilco sound like Loose Fur after officially replacing Ken Coomer with Kotche in January 2001.

Although Bennett sought to act as both mixer and engineer for Yankee Hotel Foxtrot, Tweedy was unsure of Bennett's abilities against those of O'Rourke. Tweedy and Bennett frequently argued over whether the album should be accessible to a general listener, or attempt to cover new musical ground. Unbeknownst to Bennett, Tweedy invited O'Rourke to remix "I Am Trying to Break Your Heart", and the results impressed the other band members—even Bennett. Tensions grew between Bennett and O'Rourke because Bennett wanted to mix every song on the album. O'Rourke cut the contributions of other members on several of the songs; some songs, such as "Poor Places", only featured the Loose Fur trio. The album was completed in 2001, and Bennett left the band immediately afterwards. The recording of the album was documented by Sam Jones and released in 2002 as the film I Am Trying to Break Your Heart.

Time Warner, which owned Warner Brothers, merged with America Online in 2001, leading to more pressure on Warner's record labels to cut costs. Over 600 employees of Warner Music Group were fired, including Howie Klein, the president of Reprise Records. In absence of Klein, David Kahne became the interim head of Reprise. Kahne assigned Mio Vukovic to monitor the progress of Yankee Hotel Foxtrot and to offer suggestions. Music journalist Greg Kot claims that Vukovic disdained the album and was unhappy that Wilco ignored his suggestions. He brought the album to Kahne, who felt that there was no single on the album. In June 2001, the album was rejected by Reprise and Wilco was asked to leave the label.

Wilco managed to negotiate terms to a buy-out from Reprise. Music journalist Greg Kot claims that instead of financial compensation, the band agreed to leave the label with the master tapes of Yankee Hotel Foxtrot. The label was already receiving bad publicity for its treatment of the band and were willing to accommodate Wilco's request. However, Allmusic claims that Wilco "bought the finished studio tapes from Warner/Reprise for a reported $50,000 and left the label altogether" after Wilco was "unwilling to change the album to make it more 'commercially viable.'" To curb the negative publicity, Reprise began to invest more in bands such as The Flaming Lips. Lead singer Wayne Coyne once remarked:

"We are benefiting from the label's regret over Wilco. We are living in the golden age of that being such a public mistake. The people on Warners said, 'we'll never have a band like Wilco feel we don't believe in them again.' They'd tell me that it would never happen to us. And what a great day for me!"

As the band searched for a new label to release the album, they decided to stream it at their official website to discourage illegal trading of low-quality MP3s. The band signed with Nonesuch Records, another Time Warner subsidiary, and the album was released in the spring of 2002. When it was released, Yankee Hotel Foxtrot reached number thirteen on the Billboard 200, Wilco's highest chart position to that date. Yankee Hotel Foxtrot sold over 590,000 copies, and to date remains Wilco's best selling album. Yankee Hotel Foxtrot was met with wide critical acclaim: it topped 2002's Pazz & Jop critics' poll, was named one of the 100 greatest albums of all time by Q Magazine, and was named one of the 500 Greatest Albums of All Time by Rolling Stone.

Down with Wilco, A Ghost Is Born, and Kicking Television: Live in Chicago

In November 2003, Wilco traveled to New York City to record their fifth album. Unlike Summerteeth and Yankee Hotel Foxtrot, A Ghost Is Born featured songs that were created with Pro Tools before ever performing them live. The album featured the song "Less Than You Think", which included a fifteen-minute track of electronic noises and synthesizers, which Tweedy called "the track that everyone will hate". Tweedy justified the inclusion of the song:

"I know ninety-nine percent of our fans won't like that song, they'll say its a ridiculous indulgence. Even I don't want to listen to it every time I play through the album. But the times I do calm myself down and pay attention to it, I think it's valuable and moving and cathartic. I wouldn't have put it on the record if I didn't think it was great … I wanted to make an album about identity, and within that is the idea of a higher power, the idea of randomness, and that anything can happen, and that we can't control it."

Leroy Bach left the band immediately after the album's completion to join a music theatre operation in Chicago. Like Yankee Hotel Foxtrot, Wilco streamed the album online before its commercial release. Instead of using their own web page, the band streamed it in MPEG-4 form on Apple's website. Wilco sought to substantially change their lineup after Bach's departure, and added Mikael Jorgensen, who had engineered Down with Wilco, Pat Sansone of The Autumn Defense, and avant-garde guitarist Nels Cline to the lineup. Just as the band was about to tour to promote the album, Tweedy checked himself in to a rehabilitation clinic in Chicago for an addiction to painkillers. As a result, tour plans for Europe were canceled, and the release date for the album was set back several weeks. A Ghost Is Born was released on June 22, 2004, and became Wilco's first top ten album in the U.S. The album earned Wilco Grammy Awards for Best Alternative Music Album and Best Recording Package in 2005. It also placed thirteenth on 2004's Pazz & Jop Critics Poll.

In 2004, the band released The Wilco Book, a picture book detailing the creation of A Ghost Is Born. The book also contains writings and drawings from band members, as well as a CD with demos from the A Ghost Is Born recording sessions. Also that year, Chicago Tribune music critic Greg Kot released a biography of the band entitled Wilco: Learning How to Die. The new six-piece Wilco lineup debuted on Kicking Television: Live in Chicago, a two disc live album recorded at The Vic Theater in Chicago. Released on November 15, 2005, the album received high accolades from Spin, Billboard, and Entertainment Weekly. As of 2007, it has sold over 114,000 copies.

Sky Blue Sky

Wilco returned to their loft in Chicago to record a sixth studio album in 2006. Influenced by The Byrds and Fairport Convention, the band considered Sky Blue Sky to be less experimental than previous releases. Also unlike previous albums, the songs were created as collaborations.

Wilco streamed the album online on March 3, 2007, and offered the song "What Light" as a free MP3 download. To further publicize the album, Wilco licensed several songs from the Sky Blue Sky recording sessions for use in a Volkswagen advertising campaign. The move was criticized by both critics and fans; Wilco responded by noting that they had previously done advertising campaigns with Apple Computers and Telefónica Móviles (Movistar). The album was released on May 15, 2007, and was a commercial success: it sold over 87,000 copies in its first week and peaked in the top five in the U.S. album charts. It also was a top forty hit in seven other countries.

Reviewer James Brubaker states that Wilco “shines on a handful of the songs” on Sky Blue Sky, such as the “light, and straightforward” songs. While he calls the album “great traditional rock and folk album at times”, he states that “once you get past the handful of masterful and lovely performances… the rest of the record comes off at times as dull, and forced”. The allaboutjazz review also had mixed comments. While praising the album as “deceptively insinuating, almost intoxicating to listen to” and noting its “impeccable sound quality”, the reviewer claimed that “Sky Blue Sky becomes the first Wilco album that sounds too careful for its own good.”

Pabs Hernandez, a reviewer for Lost at Sea praised the album’s “breezy atmosphere and pacing”, and noted that it is not “easily judged upon first listen.” Overall, Hernandez stated that it “may be no masterpiece, but at worst it's a more than worthy entry into Wilco's laudable catalogue.” Reviewer Greg Locke praised the record as “one of the best albums of the year”, calling it a “timeless record, full of sweet, hopeful sophistication and class” and “a lean, mean, soulful album.” Like Hernandez, Locke acknowledged that the album could not be properly judged just on the first listening. The NPR review also had a positive take on the record. While the NPR reviewer stated that the recording “isn't groundbreaking”, they praised its “coherent musical expression” and emphasis on “solid songcraft without pretense” which created a “satisfying and melodically sound albu.”

Musical style and influence

Wilco's music is typically categorized as alternative rock and alternative country. Despite their career long association with a major record label, they are generally associated with indie rock. Wilco draws influence from bands from a variety of musical genres, but primarily from music created between 1966 and 1974. John Cale's Paris 1919 was credited by the band as providing a musical parallel. According to Tweedy, "It was eye-opening that I wasn't the only person that felt like these worlds had a lot more in common than they'd been given credit for—that experimentation and avant-garde theory was not directly opposed to beauty, y'know?"

Some critics have dubbed Wilco the "American Radiohead", due to their stylistically diverse catalog. A critic from the New York Times argues that Wilco has a "roots-rock… reached back to proven materials: the twang of country, the steady chug of 1960s rock, the undulating sheen of the Beach Boys, the honky-tonk hymns of the Band and the melodic symmetries of pop."